I also use a 08 Tundra 5.7 as a DD/tow vehicle with a 20' Cargo Mate trailer. Fully loaded it drives great and is very comfortable. Bought the Tundra used at CarMax for about $8k under blue book.
What are you all using for a brake controller?
I've got an 07 Tundra that I daily and have a 20' enclosed on order that I am picking up in April. I just installed a Prodigy P3 over the weekend although havent tried it out yet. Easy install, put it between the 2 power outlets in the center console.